Methylamine → 1-[4-Fluoro-2-(methylamino)phenyl]ethanone

HRID 358662Notes

Reaction equation

HRID 358662 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4](Cl)[CH:3]=1.[CH3:12][NH2:13]>[Cu]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([NH:13][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27365072'-Chloro-4'-fluoroacetophenone

Product 1

HCID 199784601-[4-Fluoro-2-(methylamino)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 4'-fluoro-2'-chloroacetophenone (40 g), methylamine (33% w/w solution in industrial methylated spirit, 60 ml), industrial methylated spirit (40 ml) and copper powder (0.5 g) was stirred at 80° in a sealed pressure vessel for 3 hours. After cooling to ambient temperature, the reaction mixture was transferred to a conical flask. The reaction vessel was washed out with industrial methylated spirit (2×30 ml) and the washings added to the reaction mixture. Sodium sulphide nonahydrate (2.3 g) in water (23 ml) was added and the mixture heated at 50° for 10 minutes. The mixture was filtered through diatomaceous earth (sold under the trade name CELITE). Solvent was removed from the filtrate under reduced pressure at 40° and hydrochloric acid (5M, 160 ml) was added to the residue. The mixture was stirred for approximately 2 hours and then extracted with dichloromethane (100 ml, then 2×60 ml). The combined extracts were dried over magnesium sulphate and evaporated to give the novel compound 4'-fluoro-2'-(methylamino)acetophenone as an oil which solidified on storing at ambient temperature.

Workup

  1. customthe reaction mixture was transferred to a conical flask
  2. washThe reaction vessel was washed out with industrial methylated spirit (2×30 ml)
  3. additionthe washings added to the reaction mixture
  4. additionSodium sulphide nonahydrate (2.3 g) in water (23 ml) was added
  5. temperaturethe mixture heated at 50° for 10 minutes
  6. filtrationThe mixture was filtered through diatomaceous earth (
  7. customSolvent was removed from the filtrate under reduced pressure at 40°
  8. additionhydrochloric acid (5M, 160 ml) was added to the residue
  9. stirringThe mixture was stirred for approximately 2 hours
  10. extractionextracted with dichloromethane (100 ml
  11. dry with materialThe combined extracts were dried over magnesium sulphate
  12. customevaporated

Sources & evidence

ORD record
ord-8974b54a71504408b8514dedf3f1a020
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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